Lipid Structure and

Function
Pages 27-36 in textbook

Common Physical
Properties of Lipids

Soluble in non-polar organic solvents

Contain C, H, O

Includes fats and oils mostly

triglycerides

Sometimes N & P

Fat: solid at room temperature

Oil: liquid at room temperature

More highly reduced than CHO

2.25x more energy

Lipids or Glucose for

Energy?
H3C

C
H2

HC
HO

H2
C

CH
HC

HO

CH

HO

CH

OH

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

O
C
OH

Energy-Containing Nutrients (C and

ATP

Electron
Transport
Chain

H
+

CO
2

CH2OH

O2
H2O

Lipids or Glucose for

Energy?
H3C

C
H2

H2
C

HC
HO

C
H2

H2
C

CH
HC

HO

CH

HO

CH

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

O
C
OH

More reduced state (more H bound to C)

More potential for oxidation

OH

CH2OH

Less reduced state (more O bound to C)

Less potential for oxidation

Energy from Lipids

Compared to carbohydrates, fatty acids

contain more hydrogen molecules per
unit of carbon, thus, they are in a more
reduced form
Carbohydrates are partially oxidized so
they contain less potential energy (H+
and e-) per unit of carbon

Functions and Properties

Concentrated source of energy (9

kcal/gm)
Energy reserve: any excess energy from
carbohydrates, proteins and lipids are
stored as triglycerides in adipose tissues
Provide insulation to the body from cold

Maintain body temperature

Mechanical insulation

Protects vital organs

Functions and Properties

Electrical insulation

Supply essential fatty acids (EFA)

Protects nerves, help conduct electrochemical impulses (myelin sheath)

Linoleic acid and linolenic acid

Formation of cell membranes

Phospholipids, a type of fat necessary for

the synthesis of every cell membrane (also
glycoproteins and glycolipids)

Functions and Properties

Synthesis of prostaglandins from fatty acids

Hormone-like compounds that modulates many

body processes

Help transport fat soluble vitamins

Palatability and aroma

Immune system, nervous systems, and GI secretions

Regulatory functions: lower BP, blood clotting, uterine
contractions

Flavor and taste for some species!

The satiety value help control appetite

Fullness; fats are digested slower

Regulated through gastric inhibitory protein (GIP) and

cholecystokinin (CCK)

Physical Traits of Fatty

Acids

Form membranes, micelles, liposomes

Orient at water:oil interface

Contain hydrophobic and hydrophilic groups
Lipid bilayer for membranes

Micelles formed during digestion

Physical Traits of Fatty

Acids

Fatty acids form soaps with

cations

Na & K soaps water soluble

Ca & Mg soaps not water soluble

Poorly digested

Major issue in feeding fats to

ruminants

Physical Traits of Fatty

Acids

Unsaturated fatty acids oxidize

spontaneously in presence of
oxygen

Auto-oxidation, peroxidation, rancidity

Free radicals formed

Reduce nutritional value of fats

Antioxidants prevent oxidation

Vitamins C and E, selenium

=O

-H

-H

Fatty Acid Structure

Methyl
group

-H

-H

H - C - ( C )n - C - OH
Carbon
group(s
)

Carboxyl
group

Fatty Acids

With a few exceptions, natural fatty

acids:

Contain an even number of carbon atoms

Arranged in an unbranched line
Have a carboxyl group (-COOH) at one
end
Have a methyl group (CH3) at the other
end

Fatty Acid Chain Length

Short chain: 2 to 6 C (volatile fatty acids)

Medium chain: 8 12 C
Long chain: 14 24 C
As chain length increases, melting point
increases
Fatty acids synthesized by plants and
animals have an even number of carbons

Mostly long chain

16C to 18C fatty acids are most prevalent

Fatty Acid Saturation

Saturated - no double bonds

Unsaturated contain double bonds

Monounsaturated one double bond

Polyunsaturated - >1 double bond
The double bond is a point of
unsaturation

As number of double bonds

increases, melting point decreases

Saturated Fats

All the chemical bonds between the

carbon are single bonds
C-C-CNo double bonds
No space for more H atoms; fully
saturated
Solid at room temperature

Butter, shortening, lard, coconut oil, palm oil,

and fully hydrogenated vegetable oils
Poultry skin, whole milk

Mono-Unsaturated Fatty
Acids

Only one double bond

Therefore, two H atoms can be added

Liquid at room temperature

Olive oil, canola oil, peanut oil

Other sources: avocado, almonds,
cashews, pecans and sesame seeds
(tahini paste)

Poly-Unsaturated Fatty
Acids

Two or more double bonds

Include omega-3 and omega-6 fatty
acids (essential fatty acids)

Linolenic acid: omega 3 fatty acid

Linoleic acid: omega 6 fatty acid

Richest sources of poly-unsaturated

fatty acids include:

Vegetable oils

Corn, sunflower, safflower, cotton seed oils

Saturation

Unsaturated fatty acids

Converted to saturated fatty acids by rumen

microbes
More susceptible to rancidity

Oxidation of double bonds produces peroxides and free

radicals, which can cause damage to other compounds

Antioxidants

Vitamins E, C
Carotenoids

Such as beta-carotene, lycopene

Selenium

Hydrogenation of Fatty
Acids

To protect fats from becoming rancid,

poly-unsaturated fatty acids may be
hydrogenated

Increases saturation and stability - more

resistant to oxidation
Unsaturated fats entering rumen are
naturally hydrogenated (bio-hydrogenated)
Transforms the H-H configuration from cis to
trans configuration

Trans configuration alters biological availability

Trans configuration alters biological effects

Review of Fatty Acid

Nomenclature

Chain length

Most fatty acids have an equal number of

carbons

Double bonds

H3C

Fish oil is rich in odd-numbered FAs

C
H2

Number
Location from methyl or carboxyl end
Degree of saturation

H
C

C
H

H2
C

C
H

H
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature

Named according to
chain length

H3C

C
H2

C18

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature

Named according to the number of

double bonds

H3C

C
H2

C18:0

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

Common
Common name:
name:
Stearic
Stearic acid
acid

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature

Named according to the number of

double bonds

H3C

H2
C18:1

H2

C
H2

C
H2

C
H2

H2
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

Common
Common name:
name:
Oleic
Oleic acid
acid

C
H2

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature

Named according to the number of

double bonds

H3C

C
H2

C18:2
H

H2
C

C
H2

C
H

H
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

C
H2

Common
Common name:
name:
Linoleic
Linoleic acid
acid

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature

Named according to the number of

double bonds
H2
C18:3

H3C

C
H2

C
H

C
H

H
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

C
H2

Common
Common name:
name:
Linolenic
Linolenic acid
acid

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature

Named according to the

location of the first double bond
from the non-carboxyl end (count
from the methyl end)

H3C

C
H2

Omega system (e.g., omega 3, 3)

nsystem (e.g., n3)
H
C

C
H

H2
C

C
H

H
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

O
C
OH

Fatty-acid Nomenclature
H3C

C
H2

H3C

H3C

H2
C

C
H2

C
H2

H2
C

C
H2

H
C

H2
C

C
H2

C
H

C
H2

H2
C

C
H2

H
C

H2
C

C
H

C
H2

H2
C

C
H2

H2
C

Omega 9 or n9 fatty acid

H2
C

C
H

H
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

C
H2

H2
C

Omega 6 or n6 fatty acid

H2
C

C
H

H
C

C
H2

H
C

C
H

H2
C

C
H2

H2
C

C
H2

C
H2

Omega 3 or n3 fatty acid

H2
C

C
H2

H2
C

O
C
OH

H2
C

C
H2

O
C
OH

H2
C

O
C
OH

Fatty Acid Synthesis Issues

-3

-6

-9

C-C-C=C-C-C=C-C-C=C-C-C-C-C-C-C-C-COOH

Animals can synthesize a fatty acid with

a double bond in the omega 9 position
but not at either 3 or 6 positions

Omega-3 and omega-6 fatty acids must be

derived from diet

Cold water fish accumulate high levels

of omega 3 fatty acids from their diet

Omega System and

Essential Fatty
Acids

Linoleic acid is an omega-6 fatty acid

Linolenic and arachidonic acids are
omega-3 fatty acids

Linoleic and linolenic acids are essential

fatty acids
Arachidonic acid can be synthesized
from linoleic acid, so not essential

Exception is cats (of course)

Fatty-acid Nomenclature

Named according to location of

Hs

Cis or trans fatty acids

Cis-9-octadecenoic acid
(Oleic acid)

Trans-9-octadecenoic acid
(Elaidic acid)

Fatty-acid Nomenclature
H3C

C
H2

H2
C

C
H2

H2
C

C
H2

H2
C

C
H2

H
H2
C
H2
C
H2
C
H

C
3

C 2
H

C 2
H

C 2
H

H
C

H
C
C

C 2
H

C
H C
H2

C
H2

H2
C

H2
C

C
H2

C
H2
H2
C

H2
C

C
H2

C
H2
H2
C

H2
C

O
C
H2

O
C
H2

C
OH

OH

Isomers

Geometrical isomers
due to double bond

Cis

occurs naturally
bend in acyl chain

Trans

Not as common
Found in
hydrogenated oils
Results from bacterial
synthesis

In fats in
ruminants!!

Straight acyl chains

Chain branching

Straight

Synthesized by
mammals and plants

Branched

Synthesized by
bacteria

Cis Fatty Acids

Melting Points

Affected by chain length

Longer chain = higher melting temp

Fatty acid:
C12:0
Melting point: 44C

C14:0
58C

C16:0
63C

C18:0
72C

C20:0
77C

Which fatty acids are liquid at room temperature?

Which fatty acids are solid at room temperature?

Chain Length

In most fats with a mixture of fatty acids, the

chain length of the majority of fatty acids will
determine the hardness of the fat

<10 carbons = liquid

Between 10 and 20 carbons = ???
>20 carbons = solid

Acetic Acid (2 C)

Vinegar

Liquid

Stearic Acid (18 C)

Beef Tallow

Solid

Arachidic Acid (20

C)

Butter

Solid

Melting Points

Affected by number of double bonds

More saturated = higher melting temp

Fatty acid:
Melting point:

C18:0
72C

C18:1
16C

C18:2
5C

C18:3
11C

Which fatty acid is liquid at room temperature?

Which fatty acids are solid at room temperature?

Carbons Double
bonds

Abbreviation

Source

2:0

bacterial
metabolism

3:0

bacterial
metabolism

Butyric

4:0

butterfat

Caproic

6:0

butterfat

Caprylic

8:0

coconut oil

Capric

10

10:0

coconut oil

Lauric

12

12:0

coconut oil

Myristic

14

14:0

palm kernel oil

Palmitic

16

16:0

palm oil

Palmitoleic

16

16:1

animal fats

Stearic

18

18:0

animal fats

Oleic

18

18:1

olive oil

Linoleic

18

18:2

grape seed oil

Linolenic

18

18:3

flaxseed (linseed) oil

Arachidonic

20

20:4

peanut oil, fish oil

Acids
Acetic
Propionic

Essential Fatty Acids

Must be in diet

Tissues can not synthesize

Linoleic acid (18:2)

Linolenic acid (18:3)

Omega-6-FA
Omega-3-FA

Arachidonic (20:4)

Not found in plants!

Can be synthesized from C18:2 (linoleic acid) in
most mammals (except in cat)

Essential nutrient in the diet of cats

Functions of
Essential Fatty
Acids
A component of the phospholipids

in cell membranes
Precursor for prostaglandins:
arachidonic acid
Important metabolic regulator

Contraction of smooth muscle

Aggregation of platelets
Inflammation

Arachidonic Acid

Prostaglandins

Thrombocyclin
Prostacyclin
Leukotrenes
Neurotransmitters
Cychrome P450

Synthesized in liver

elongates linoleic acid (C18:2)

Essential Fatty Acids

Since dietary poly-unsaturated fatty

acids are hydrogenated to saturated
fatty acids in the rumen by the
microbes, how do ruminants meet
their essential fatty acid requirement?

By-pass (rumen protected) lipids

Microbial lipid synthesis

Microbes dont utilize lipids for energy, but

they do synthesize them for their cell
membranes

Essential Fatty Acids

Deficiency of essential fatty acid

intakes:

Growth retardation
Problems with reproduction
Skin lesions
Kidney and liver disorders

Simple Lipids

Neutral fats and oils

Monoacyl glycerols (monoglycerides)

Diacyl glycerols (diglycerides)
Diglycerides found in plant leaves

One fatty acid is replaced by a sugar (galactose)

Triacyl glycerols (triglycerides)

Triglycerides found in seeds and

animal adipose tissue

Triacyl glycerols (triglycerides)

Lipid storage form

Where in the body? Adipocytes!!

Most lipids consumed are triglycerides

Triglycerides

Most common structure in dietary lipids

Composed of one glycerol molecule and three fatty
acids connected by an ester bond (bond between
an alcohol and and organic acid)

Fatty acids may be same or mixed

Fatty
Acid
Fatty
Acid

Glycero
l
Fatty Acid

Triglyceride Structure

Fatty acid composition of triglyceride varies

according to function

Membrane lipids must be fluid at all

temperatures

Lipids in tissues subjected to cooling

(e.g., hibernators or tissues in extremities)

Contain more unsaturated fatty acids

Contain more unsaturated FAs

Butterfat (milk fat) is fairly fluid

in spite of containing mostly saturated FAs

Why? Chain length!!

Most Common Fatty Acids

in
Diand
Triglycerides
Fatty acid
Carbon:Double bonds
Double bonds
Myristic

14:0

Palmitic

16:0

Palmitoleic

16:1

Stearic

18:0

Oleic

18:1

Cis-9

Linoleic

18:2

Cis-9,12

Linolenic

18:3

Cis-9,12,15

Arachidonic

20:4

Cis-5,8,11,14

Eicosapentaenoic

20:5

Cis-5,8,11,14,17

Docosahexaenoic

22:6

Cis-4,7,10,13,16,19

CH3(CH2)nCOOH

Cis-9

Complex Lipids Phospholipids

Two primary types:

Glycerophosphatides

Core structure is glycerol

Part of cell membranes, chylomicrons,
lipoproteins

Sphingophosphatides

Core structure is sphingosine

Part of sphingomyelin

Complex Lipids Phospholipids

Glycerophosphatides resemble

triglyceride in structure except one of

the fatty acids is replaced by a
compound containing a phosphate
group, or occasionally, nitrogen
Most prevalent is lecithin

Phospholipids

Significant use in feed industry as

emulsifiers

Lipids form emulsion in water

Phospholipid sources:

Liver, egg yolk,

Soybeans, wheat germ
Peanuts

Complex Lipids Glycolipids

Carbohydrate component in
structure
Cerebrosides & gangliosides

Medullary sheaths of nerves; white

matter of brain

Derived Lipids

Prostaglandins

Synthesized from arachidonic acid

Steroids

Several metabolic functions

Cholesterol, ergosterol, bile acids

Terpenes

Made by plants

Carotenoids, xanthophylls

Sterols

Compounds with multi-ring structure

Insoluble in water
Present both in plant and animal foods
Major sterol is cholesterol

However, cholesterol is found only in animal

products (manufactured in liver)

High content in organ meats and egg yolk

Common Sterol
Compounds

Cholester
ol
(a sterol)

Testosterone
(a steroid
hormone)

Vitamin D3
(cholecalcifero
l)

Stigmasterol
(a phytosterol)